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dc.contributor.advisorWorden, Leonard R.
dc.contributor.authorMayers, Dale J.
dc.descriptioniv, 13 p.en_US
dc.description.abstractThe present work was undertaken to develop a high yield synthesis of 8-methoxypsoralene. The proposed synthesis begins with pyrogallol, which is,methylated with dimethyl sulfate to form 1,2,3-trirnethoxybenzene (XII). This is brominated to form 1,5-dibromo-2,3,4-trlmethoxybenzene (XIII), which is converted to 5-brorno-2, 3,4-trlmethoxybenzaldehyde (XIV) with n-butyllithium and N,N-dimetylformamide at acetone- dry ice, temperatures. The methoxy group ortho to the formyl group is then selectively cleaved with boron trichloride forming 5-bromo-3,4-dimethoxysalicylaldehyde (XV). Overnight reflux with ethyl promoacetate (or methyl bromoacetate) and anhydrous potassium carbonate in reagent grade acetone gives ethyl (or methyl). (4'-bromo-2' ,3'-dlmethoxy-6'-formyl-phenoxyacetate (XVI) which is hydrolyzed to give the .acid (XVII). Cyclization,to 5-bromo-6,7-dlmethoxybenzofuran(XVIII) is done by reflux with acetic acid, acetic, anhydride and sodium acetate. Treatment with n-butyllithium and N,N-dlmethylformamide gives 6,7-dimethyoxy-5-formylbenzofuran (XIX), Cleavage with boron trichloride gives 6-hydroxy7-methoxy-5-formylbenzofuran(XX). The final ring closure to 8-methoxypsoralene is done by reflux with acetic anhydride and sodium acetic.en_US
dc.publisherKalamazoo Collegeen_US
dc.relation.ispartofKalamazoo College Chemistry Senior Individualized Projects Collection
dc.relation.ispartofseriesSenior Individualized Projects. Chemistry.;
dc.rightsU.S. copyright laws protect this material. Commercial use or distribution of this material is not permitted without prior written permission of the copyright holder. All rights reserved.
dc.titleA New Synthesis of 8-Methoxypsoraleneen_US

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    This collection includes Senior Individualized Projects (SIP's) completed in the Chemistry Department. Abstracts are generally available to the public, but PDF files are available only to current Kalamazoo College students, faculty, and staff.

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